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Design, Synthesis, and Anti-Proliferative Activity of Quinoxaline Linked 1,2,4-Oxadiazole Hybrids

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Abstract

Herein, synthesis of some new quinoxaline-1,2,4-oxadiazole derivatives is presented, and their in vitro anti-cancer activity against four human cancer cell lines like MCF-7 (human breast), HeLa (human cervical), HCT116 (human colon carcinoma) HepG2 (liver hepato cellular carcinoma) is tested. The results reveal promising results for four products. One of the products displays higher activity against all tested cell lines than the standard drug etoposide. Molecular docking studies of the products on EGFR receptor suggest that the most potent compound strongly binds to protein EGFR (pdbid: 4HJO). Two compounds exhibit promising inhibitory activity of tyrosine kinase EGFR.

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REFERENCES

  1. Vitale, R.M., Gatti, M., Carbone, M., Barbieri, F., Felicita, V., Gavagnin, M., Florio, T., and Amodeo, P.A., ACS Chem. Biol., 2013, vol. 8, p. 2762. https://doi.org/10.1021/cb400521b

    Article  CAS  PubMed  Google Scholar 

  2. Zhang, L., Jiang, C.S., Gao, L.X., Gong, J.X., Wang, Z.H., Li, J.Y., Li, J., Li, X.W., and Guo, Y.W., Bioorg. Med. Chem. Lett., 2016, vol. 26, p. 778. https://doi.org/10.1016/j.bmcl.2015.12.097

    Article  CAS  PubMed  Google Scholar 

  3. Zhang, H.Z., Kasibhatla, S., Kuemmerle, J., Kemnitzer, W., Ollis-Mason, K., Qiu, L., Crogan-Grundy, C., Tseng, B., Drewe, J., and Cai, S.X., J. Med. Chem., 2005, vol. 48, p. 5215. https://doi.org/10.1021/jm050292k

    Article  CAS  PubMed  Google Scholar 

  4. Pace, A., Buscemi, S., Piccionello, A.P., and Pibiri, I., Cambridge, MA, USA, 2015, vol. 116, p. 85.

  5. Rasool, I., Ahmad, M., Khan, Z.A., Mansha, A., Maqbool, T., Zahoor, A.F., and Aslam, S., Trop. J. Pharm. Res., 2017, vol. 16, p. 723.

    Article  CAS  Google Scholar 

  6. Maftei, C.V., Fodor, E., Jones, P.G., Daniliuc, C.G., Franz, M.H., Kelter, G., Fiebig, H.H., Tamm, M., and Neda, I., Tetrahedron, 2016, vol. 72, p. 1185. https://doi.org/10.1016/j.tet.2016.01.011

    Article  CAS  Google Scholar 

  7. Zaimoku, H., Taniguchi, T., and Ishibashi, H., Org. Lett., 2012, vol. 14, p. 1656.

    Article  CAS  PubMed  Google Scholar 

  8. Galal, S.A., Abdelsamie, A.S., Soliman, S.M., Mortier, J., Wolber, G., Ali, M.M., Tokuda, H., Suzuki, N., Lida, A., Ramadan, R.A., and El Diwani, H.I., Eur. J. Med. Chem. 2013, vol. 69, p. 115. https://doi.org/10.1016/j.ejmech.2013.07.049

  9. El-Enany, M.M., Kamel, M.M., Khalil, O.M., and El-Nassan, H.B., Eur. J. Med. Chem., 2010, vol. 45, p. 5286. https://doi.org/10.1016/j.ejmech.2010.08.048

    Article  CAS  PubMed  Google Scholar 

  10. Ahmed, H.E.A., Ihmaid, S.K., Omar, A.M., Shehata, A.M., Rateb, H.S., Zayed, M.F., Ahmed, S., and Elaasser, M.M., Bioorg. Chem., 2018, vol. 76, p. 332. https://doi.org/10.1016/j.bioorg.2016.02.007

    Article  CAS  PubMed  Google Scholar 

  11. Gediya, L.K. and Njar, V.C., Expert Opin. Drug Discov., 2009, vol. 4, p. 1099. https://doi.org/10.1517/17460440903341705

    Article  CAS  PubMed  Google Scholar 

  12. Huang, X. and Cheng-Chu, C., Synthesis, 1984, vol. 6, p. 851. https://doi.org/10.1021/acs.Orglett.7b01025

    Article  Google Scholar 

  13. Tron, G.C., Pirali, T., Billington, R.A., Canonico, P.L., and Sorba, G., Med. Res. Rev., 2008, vol. 28, p. 278. https://doi.org/10.1002/med.20107

    Article  CAS  PubMed  Google Scholar 

  14. Mc Bryan, J., Howlin, J., Napoletano, S., and Martin, F., J. Mammary Gland Biol. Neoplasia, 2008, vol. 13, p. 159. https://doi.org/10.1007/s10911-008-9075-7

    Article  Google Scholar 

  15. Roskoski, Jr.R., Pharmacol Res., 2014, vol. 79, p. 34. https://doi.org/10.1016/j.phrs.2019.104609

    Article  CAS  PubMed  Google Scholar 

  16. Sebastian, J., Richards, R.G., Walker, M.P., Wiesen, J.F., Werb, Z., Derynck, R., Hom, Y.K., Cunha, G.R., and Di Augustine, R.P., Cell Grow. Diff., 1998, vol. 9, p. 777.

    CAS  Google Scholar 

  17. Walker, F., Abramowitz, L., Benabderrahmane, D., Duval, X., Descatoire, V., Henin, D., Lehy, T., and Aparicio, T., Hum. Path., 2009, vol. 40, p. 1517. https://doi.org/10.1016/j.humpath.2009.05.010

    Article  CAS  PubMed  Google Scholar 

  18. Park, J.H. and Lemmon, M.A., Biochem. J., 2012, vol. 448, p. 417. https://doi.org/10.1042/BJ20121513

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Chaitanya (Deemed to be University), Kishanpura, 506001, Warangal, India

    Vinitha Badithapuram, Satheesh Kumar Nukala, Narasimha Swamy Thirukovela, Ravinder Manchal, Gouthami Dasari & Srinivas Bandari

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  1. Vinitha Badithapuram
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  2. Satheesh Kumar Nukala
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  3. Narasimha Swamy Thirukovela
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  4. Ravinder Manchal
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Correspondence to Srinivas Bandari.

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Badithapuram, V., Nukala, S.K., Thirukovela, N.S. et al. Design, Synthesis, and Anti-Proliferative Activity of Quinoxaline Linked 1,2,4-Oxadiazole Hybrids. Russ J Gen Chem 92, 117–124 (2022). https://doi.org/10.1134/S1070363222010169

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